Citation: ZHUO Lin-Sheng, DONG Huan, HUANG Wei, ZHAO Xing-E, SHE Neng-Fang. Synthesis, Crystal Structure and Biological Activity of 8-((4-((2,3-diaminopyridin-4-yl)oxy)-3-fluorophenyl)-amino)-2-(4-fluorophenyl)-3-methyl-2,7-naphthyridin-1(2H)-one[J]. Chinese Journal of Structural Chemistry, ;2014, 33(6): 859-864. shu

Synthesis, Crystal Structure and Biological Activity of 8-((4-((2,3-diaminopyridin-4-yl)oxy)-3-fluorophenyl)-amino)-2-(4-fluorophenyl)-3-methyl-2,7-naphthyridin-1(2H)-one

a.
a. Key Laboratory of Pesticide and Chemical Biology of Ministry of Education of China, College of Chemistry, Central China Normal University, Wuhan 430079, China;
b.
b. College of Plant Science & Technology, Huazhong Agricultural University, Wuhan 430070, China;
c.
c. Jiangsu Key Laboratory of Molecular Targeted Antitumor Drug Research, Jiangsu Simcere Pharmaceutical Co. Ltd, Nanjing 210042, China

Received Date: 4 December 2013
Available Online: 19 December 2013
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21272086) (No. 21272086)

The new title compound 8-((4-((2,3-diaminopyridin-4-yl)-oxy)-3-fluorophenyl)-amino)-2-(4-fluorophenyl)-3-methyl-2,7-naphthyridin-1(2H)-one (C₂₆H₂₀F₂N₆O₂, M_r=486.48) has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic, space group P2₁/c with a=15.365(3), b=13.144(2), c=11.863(2)Å, β=108.882(3)°, Z=4, V=2267.0(7)Å³, D_c=1.425 g/cm³, F(000)=1008, μ=0.105 mm^-1, MoKa radiation (λ=0.71073Å), R=0.0480 and wR=0.1294 for 3197 observed reflections with I>2σ(I). X-ray diffraction analysis reveals that the region C (substituents of 8-amino group and 3-methyl group on the 2,7-naphthyridin-1(2H)-one ring) of compound 6 are effectively planar. Intramolecular and intermolecular hydrogen bonds together with π…π interations are found in the structure. In addition, compound 6 shows potent c-Met and c-Kit kinase inhibition activities.
- naphthyridine,
- crystal structure,
- synthesis,
- c-Met inhibitor
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